BR112021005936A2 - moduladores de monoacilglicerol lipase - Google Patents

moduladores de monoacilglicerol lipase Download PDF

Info

Publication number: BR112021005936A2
Authority: BR; Brazil
Prior art keywords: methyl; hexahydro; pyrazol; methanone; trifluorophenyl
Prior art date: 2018-09-28

Application number

BR112021005936-9A

Other languages

English (en)

Portuguese (pt)

Inventor

Michael K. Ameriks

Gang Chen

Chaofeng Huang

Brian Ngo Laforteza

Suchitra Ravula

Wei Zhang

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2018-09-28

Filing date

2019-09-27

Publication date

2021-06-29

2019-09-27 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2021-06-29 Publication of BR112021005936A2 publication Critical patent/BR112021005936A2/pt

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102000005398 Monoacylglycerol Lipase Human genes 0.000 title description 64
108020002334 Monoacylglycerol lipase Proteins 0.000 title description 64
150000001875 compounds Chemical class 0.000 claims abstract description 555
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 81
238000000034 method Methods 0.000 claims abstract description 77
201000010099 disease Diseases 0.000 claims abstract description 41
208000035475 disorder Diseases 0.000 claims abstract description 40
206010028980 Neoplasm Diseases 0.000 claims abstract description 16
208000002193 Pain Diseases 0.000 claims abstract description 16
208000020401 Depressive disease Diseases 0.000 claims abstract description 10
208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims abstract description 5
230000000926 neurological effect Effects 0.000 claims abstract 3
-1 O-C1-4 haloalkyl Chemical group 0.000 claims description 519
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 329
125000000217 alkyl group Chemical group 0.000 claims description 158
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 101
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 101
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
125000001188 haloalkyl group Chemical group 0.000 claims description 77
150000003839 salts Chemical class 0.000 claims description 67
229910052757 nitrogen Inorganic materials 0.000 claims description 47
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 46
239000012453 solvate Substances 0.000 claims description 44
125000001072 heteroaryl group Chemical group 0.000 claims description 37
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 35
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 34
125000001424 substituent group Chemical group 0.000 claims description 34
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 28
125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 27
238000011282 treatment Methods 0.000 claims description 27
229910052731 fluorine Inorganic materials 0.000 claims description 24
239000008194 pharmaceutical composition Substances 0.000 claims description 22
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
102000005962 receptors Human genes 0.000 claims description 20
108020003175 receptors Proteins 0.000 claims description 20
SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims description 19
239000000546 pharmaceutical excipient Substances 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
230000000694 effects Effects 0.000 claims description 18
125000004076 pyridyl group Chemical group 0.000 claims description 18
125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
230000001404 mediated effect Effects 0.000 claims description 17
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 10
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 10
102100029814 Monoglyceride lipase Human genes 0.000 claims description 9
208000020925 Bipolar disease Diseases 0.000 claims description 8
101100113485 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chs-3 gene Proteins 0.000 claims description 8
239000008186 active pharmaceutical agent Substances 0.000 claims description 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 7
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 7
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 7
206010065390 Inflammatory pain Diseases 0.000 claims description 6
229910000831 Steel Inorganic materials 0.000 claims description 6
208000024714 major depressive disease Diseases 0.000 claims description 6
VUAOIXANWIFYCU-UHFFFAOYSA-N quinoline-6-carbaldehyde Chemical compound N1=CC=CC2=CC(C=O)=CC=C21 VUAOIXANWIFYCU-UHFFFAOYSA-N 0.000 claims description 6
239000010959 steel Substances 0.000 claims description 6
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000004553 quinoxalin-5-yl group Chemical group N1=CC=NC2=C(C=CC=C12)* 0.000 claims description 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
JYFNTDPGDPZMCM-UHFFFAOYSA-N 1-hydroxy-2-nonylquinolin-4-one Chemical compound C1=CC=C2N(O)C(CCCCCCCCC)=CC(=O)C2=C1 JYFNTDPGDPZMCM-UHFFFAOYSA-N 0.000 claims description 2
HRHJSKLWNMFXBF-UHFFFAOYSA-N 1-phenyl-1,2,4-triazole-3-carbaldehyde Chemical compound N1=C(C=O)N=CN1C1=CC=CC=C1 HRHJSKLWNMFXBF-UHFFFAOYSA-N 0.000 claims description 2
JSBWLHLFMAMYPJ-UTKZUKDTSA-N 3,4-dihydro-1H-isochromen-7-yl-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound C1OCCC2=CC=C(C=C12)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 JSBWLHLFMAMYPJ-UTKZUKDTSA-N 0.000 claims description 2
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 2
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
101000980673 Homo sapiens Multicilin Proteins 0.000 claims description 2
241000188250 Idas Species 0.000 claims description 2
102100024179 Multicilin Human genes 0.000 claims description 2
PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 claims description 2
YFLJTQLASQZXJD-UTKZUKDTSA-N [1-(4-fluorophenyl)-5-methyl-1,2,4-triazol-3-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC1=CC=C(C=C1)N1N=C(N=C1C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 YFLJTQLASQZXJD-UTKZUKDTSA-N 0.000 claims description 2
229910052789 astatine Inorganic materials 0.000 claims description 2
125000005605 benzo group Chemical group 0.000 claims description 2
125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims description 2
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 2
UGOIXUFOAODGNI-UHFFFAOYSA-N quinoxaline-6-carbaldehyde Chemical compound N1=CC=NC2=CC(C=O)=CC=C21 UGOIXUFOAODGNI-UHFFFAOYSA-N 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 42
YSSRHSKEUIONEB-PELKAZGASA-N (1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-diene Chemical compound [H][C@]12CC[C@]([H])(N1)C1=NN(C)C(=C1C2)C1=CC(F)=C(F)C(F)=C1 YSSRHSKEUIONEB-PELKAZGASA-N 0.000 claims 2
ZIYVWOCHDPPRQB-APWZRJJASA-N (2-chloro-3-methoxyphenyl)-[(1S,8R)-4-methyl-5-phenyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC1=C(C=CC=C1OC)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC=CC=C3)C)[C@@H]1CCC2 ZIYVWOCHDPPRQB-APWZRJJASA-N 0.000 claims 2
IWNNQGNSNBDJHT-UHFFFAOYSA-N 5-methoxy-1-methylpyrazole-4-carbaldehyde Chemical compound COC1=C(C=O)C=NN1C IWNNQGNSNBDJHT-UHFFFAOYSA-N 0.000 claims 2
CLLSRYUCUFLWKX-VFNWGFHPSA-N [4-methoxy-2-(triazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=CC(=C(C=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 CLLSRYUCUFLWKX-VFNWGFHPSA-N 0.000 claims 2
VMSHGFHYFZVTSU-VFNWGFHPSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=CC(=C(C=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 VMSHGFHYFZVTSU-VFNWGFHPSA-N 0.000 claims 2
125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims 2
JSTMUBIVINYHMT-ACJLOTCBSA-N (1,5-dimethylpyrazol-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CN1N=CC(=C1C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 JSTMUBIVINYHMT-ACJLOTCBSA-N 0.000 claims 1
GWCNNMCJPPEJPT-ACJLOTCBSA-N (1-methylpyrazolo[3,4-b]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CN1N=C(C=2C1=NC=CC=2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 GWCNNMCJPPEJPT-ACJLOTCBSA-N 0.000 claims 1
OKULNJZMDNWODB-YJYMSZOUSA-N (1-methylpyrazolo[3,4-b]pyridin-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CN1N=CC=2C1=NC=CC=2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 OKULNJZMDNWODB-YJYMSZOUSA-N 0.000 claims 1
GPWZUDCSWJWCBM-PXAZEXFGSA-N (1-methylpyrazolo[3,4-d]pyrimidin-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CN1N=CC=2C1=NC=NC=2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 GPWZUDCSWJWCBM-PXAZEXFGSA-N 0.000 claims 1
UYMQHMRVZALWRL-YJYMSZOUSA-N (1-methylpyrrolo[2,3-b]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound CN1C=C(C=2C1=NC=CC=2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 UYMQHMRVZALWRL-YJYMSZOUSA-N 0.000 claims 1
DDLKOLSDQUNKHU-VLIAUNLRSA-N (1-methylpyrrolo[2,3-b]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CN1C=C(C=2C1=NC=CC=2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 DDLKOLSDQUNKHU-VLIAUNLRSA-N 0.000 claims 1
HBAQDEJGMLYXRY-VLIAUNLRSA-N (1-methylpyrrolo[2,3-b]pyridin-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CN1C=CC=2C1=NC=CC=2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 HBAQDEJGMLYXRY-VLIAUNLRSA-N 0.000 claims 1
JSWQAKAHMKOWGM-ACJLOTCBSA-N (2,3-dimethoxyphenyl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound COC1=C(C=CC=C1OC)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 JSWQAKAHMKOWGM-ACJLOTCBSA-N 0.000 claims 1
SIQIHHMTAWFMGQ-BEFAXECRSA-N (2,5-dimethylimidazo[1,2-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound CC=1N=C2N(C(=CC=C2)C)C=1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 SIQIHHMTAWFMGQ-BEFAXECRSA-N 0.000 claims 1
NIXVJSLRIHRSGV-BEFAXECRSA-N (2,6-dimethylimidazo[1,2-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound CC=1N=C2N(C=C(C=C2)C)C=1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 NIXVJSLRIHRSGV-BEFAXECRSA-N 0.000 claims 1
SNWXFJBSGGNIDS-UZLBHIALSA-N (2,7-dimethylimidazo[1,2-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC=1N=C2N(C=CC(=C2)C)C=1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 SNWXFJBSGGNIDS-UZLBHIALSA-N 0.000 claims 1
VYGUZLXROVRBEK-BEFAXECRSA-N (2,7-dimethylimidazo[1,2-b]pyridazin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC=1N=C2N(N=CC(=C2)C)C=1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 VYGUZLXROVRBEK-BEFAXECRSA-N 0.000 claims 1
ANEHJIIOBFCNGB-QRWLVFNGSA-N (2,7-dimethylpyrazolo[1,5-a]pyrimidin-5-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC1=NN2C(N=C(C=C2C)C(=O)N2[C@H]3CC=4C(=NN(C=4C4=CC(=C(C(=C4)F)F)F)C)[C@@H]2CCC3)=C1 ANEHJIIOBFCNGB-QRWLVFNGSA-N 0.000 claims 1
OQEOJLWLRWDGGS-APWZRJJASA-N (2-amino-1,3-benzoxazol-6-yl)-[(1S,8R)-5-(3,5-difluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound NC=1OC2=C(N=1)C=CC(=C2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC(=C3)F)F)C)[C@@H]1CCC2 OQEOJLWLRWDGGS-APWZRJJASA-N 0.000 claims 1
TTYTYEPMUUULHR-XCLFUZPHSA-N (2-fluoro-4-methoxyphenyl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC1=C(C=CC(=C1)OC)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 TTYTYEPMUUULHR-XCLFUZPHSA-N 0.000 claims 1
RXKCPUIGFQDHLL-ZHRRBRCNSA-N (2-imidazol-1-ylphenyl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound N1(C=NC=C1)C1=C(C=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 RXKCPUIGFQDHLL-ZHRRBRCNSA-N 0.000 claims 1
AHFXOBXKMMUQFY-VLIAUNLRSA-N (2-methylindazol-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CN1N=C2C=CC=CC2=C1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 AHFXOBXKMMUQFY-VLIAUNLRSA-N 0.000 claims 1
GPCOCNPXJURKLO-PXAZEXFGSA-N (3-chloro-2-methoxypyridin-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC=1C(=NC=CC=1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)OC GPCOCNPXJURKLO-PXAZEXFGSA-N 0.000 claims 1
YNZSLNYIBIKCMQ-DIFFPNOSSA-N (3-chloro-5-fluoropyridin-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC=1C=NC=C(C=1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)F YNZSLNYIBIKCMQ-DIFFPNOSSA-N 0.000 claims 1
LYVXQMJKAGWYOQ-QRWLVFNGSA-N (3-chloro-5-methoxyphenyl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC=1C=C(C=C(C=1)OC)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 LYVXQMJKAGWYOQ-QRWLVFNGSA-N 0.000 claims 1
PLIJASLKQKWUQR-KDOFPFPSSA-N (3-chlorophenyl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound ClC=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 PLIJASLKQKWUQR-KDOFPFPSSA-N 0.000 claims 1
WTVJKYYXGHSAQJ-WBMJQRKESA-N (3-fluoro-1,5-dimethylpyrazol-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC1=NN(C(=C1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)C)C WTVJKYYXGHSAQJ-WBMJQRKESA-N 0.000 claims 1
LVIGGIBAJSAOPT-VGSWGCGISA-N (3-fluoro-5-pyrazol-1-ylphenyl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=C(C=C(C=1)N1N=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 LVIGGIBAJSAOPT-VGSWGCGISA-N 0.000 claims 1
MDFFCSOQJKECLA-PXAZEXFGSA-N (3-methoxy-1-methylpyrazol-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=NN(C=C1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)C MDFFCSOQJKECLA-PXAZEXFGSA-N 0.000 claims 1
IXWYYIMBPPDZGX-XCLFUZPHSA-N (3-methoxyphenyl)-[(1S,8R)-4-methyl-5-(2,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound COC=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=C(C=C(C(=C3)F)F)F)C)[C@@H]1CC2 IXWYYIMBPPDZGX-XCLFUZPHSA-N 0.000 claims 1
NZJIXLFWCWJPHA-KUHUBIRLSA-N (3-methoxyphenyl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound COC=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 NZJIXLFWCWJPHA-KUHUBIRLSA-N 0.000 claims 1
AYTVIBWMKNIZOS-IERDGZPVSA-N (3-methyl-5-propan-2-ylpyrazolo[1,5-a]pyrimidin-7-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound C(C)(C)C1=NC=2N(C(=C1)C(=O)N1[C@H]3CC=4C(=NN(C=4C4=CC(=C(C(=C4)F)F)F)C)[C@@H]1CCC3)N=CC=2C AYTVIBWMKNIZOS-IERDGZPVSA-N 0.000 claims 1
HPNWDHDDCVRIPG-JPYJTQIMSA-N (4-bromoquinolin-6-yl)-[(1S,8R)-5-(3,5-difluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound BrC1=CC=NC2=CC=C(C=C12)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC(=C3)F)F)C)[C@@H]1CCC2 HPNWDHDDCVRIPG-JPYJTQIMSA-N 0.000 claims 1
APEKZRRGJPOOTR-ACJLOTCBSA-N (4-chloro-2-methylpyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC1=C(C(=NC=C1)C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 APEKZRRGJPOOTR-ACJLOTCBSA-N 0.000 claims 1
YNAYEVBYYNJYNJ-ACJLOTCBSA-N (4-chloro-5-methylpyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC1=C(C=NC=C1C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 YNAYEVBYYNJYNJ-ACJLOTCBSA-N 0.000 claims 1
CCXYIPREYDZNPJ-YJYMSZOUSA-N (4-fluoropyrazolo[1,5-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=2N(C=CC=1)N=CC=2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 CCXYIPREYDZNPJ-YJYMSZOUSA-N 0.000 claims 1
VLOALLLVJWLFOC-KUHUBIRLSA-N (4-methoxy-1-methylindazol-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=C2C(=NN(C2=CC=C1)C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 VLOALLLVJWLFOC-KUHUBIRLSA-N 0.000 claims 1
IYMMEIPWFRVFNU-QRWLVFNGSA-N (4-methoxy-5-pyrazol-1-ylpyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=C(C=NC=C1N1N=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 IYMMEIPWFRVFNU-QRWLVFNGSA-N 0.000 claims 1
NEJLNCPINLSJBO-KUHUBIRLSA-N (4-methoxypyrazolo[1,5-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C=2N(C=CC=1)N=CC=2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 NEJLNCPINLSJBO-KUHUBIRLSA-N 0.000 claims 1
ZKONBDSQJCFLDX-APWZRJJASA-N (5-aminopyridin-2-yl)-[(1S,8R)-5-(3,5-difluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound NC=1C=CC(=NC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC(=C3)F)F)C)[C@@H]1CCC2 ZKONBDSQJCFLDX-APWZRJJASA-N 0.000 claims 1
YFBAYGFXJJKJHM-DYVFJYSZSA-N (5-chloro-2-methylimidazo[1,2-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound ClC1=CC=CC=2N1C(=C(N=2)C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 YFBAYGFXJJKJHM-DYVFJYSZSA-N 0.000 claims 1
XLYSMZFYUJDHMF-XIKOKIGWSA-N (5-chloro-6-methoxypyridin-2-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC=1C=CC(=NC=1OC)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 XLYSMZFYUJDHMF-XIKOKIGWSA-N 0.000 claims 1
BBHNQOMBKUQJJV-YJYMSZOUSA-N (5-ethyl-1-methylpyrazol-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound C(C)C1=C(C=NN1C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 BBHNQOMBKUQJJV-YJYMSZOUSA-N 0.000 claims 1
HYSXIWDYJLRTAD-ACJLOTCBSA-N (5-fluoro-2-methoxypyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=C(C(=NC=1)OC)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 HYSXIWDYJLRTAD-ACJLOTCBSA-N 0.000 claims 1
UQCMUCZOOFDMGE-ZHRRBRCNSA-N (5-fluoro-2-pyrazol-1-ylphenyl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=CC(=C(C=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=C1 UQCMUCZOOFDMGE-ZHRRBRCNSA-N 0.000 claims 1
BNXCHABRCAFVOU-ACJLOTCBSA-N (5-fluoro-6-methoxypyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=C(C=NC=1OC)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 BNXCHABRCAFVOU-ACJLOTCBSA-N 0.000 claims 1
GNBSGWXOHPVJKB-PXAZEXFGSA-N (5-methoxy-1-methylpyrazol-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=C(C=NN1C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 GNBSGWXOHPVJKB-PXAZEXFGSA-N 0.000 claims 1
FBACIAVAIHWSAM-UZLBHIALSA-N (5-methoxy-1-phenyl-1,2,4-triazol-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=NC(=NN1C1=CC=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 FBACIAVAIHWSAM-UZLBHIALSA-N 0.000 claims 1
KVIRCWNPBNGNGJ-KUHUBIRLSA-N (5-methoxy-4-methylpyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C(=C(C=NC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)C KVIRCWNPBNGNGJ-KUHUBIRLSA-N 0.000 claims 1
MNHDNBUQUVXVNE-YJYMSZOUSA-N (5-methoxypyridin-2-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C=CC(=NC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 MNHDNBUQUVXVNE-YJYMSZOUSA-N 0.000 claims 1
BRGULWTXWYMWDG-ZHRRBRCNSA-N (6-cyclopropyl-2-methylpyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound C1(CC1)C1=CC=C(C(=N1)C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 BRGULWTXWYMWDG-ZHRRBRCNSA-N 0.000 claims 1
GOPCRFISLSUSLN-VLIAUNLRSA-N (6-fluoropyrazolo[1,5-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=CC=2N(C=1)N=CC=2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 GOPCRFISLSUSLN-VLIAUNLRSA-N 0.000 claims 1
AUAXYJJIFZPFBV-UZLBHIALSA-N (6-imidazol-1-ylpyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound N1(C=NC=C1)C1=CC=C(C=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 AUAXYJJIFZPFBV-UZLBHIALSA-N 0.000 claims 1
SPPWHSGBNMUREF-BEFAXECRSA-N (6-methoxy-5-methylpyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=C(C=C(C=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)C SPPWHSGBNMUREF-BEFAXECRSA-N 0.000 claims 1
AEVASBPXRFRPDB-XCLFUZPHSA-N (6-methoxypyrazolo[1,5-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound COC=1C=CC=2N(C=1)N=CC=2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 AEVASBPXRFRPDB-XCLFUZPHSA-N 0.000 claims 1
HHLUQRDNNRCZML-SZNDQCEHSA-N (6-methoxypyrazolo[1,5-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C=CC=2N(C=1)N=CC=2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 HHLUQRDNNRCZML-SZNDQCEHSA-N 0.000 claims 1
BLDUWDCDVXOKAL-PXAZEXFGSA-N (6-methoxypyridin-2-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound COC1=CC=CC(=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 BLDUWDCDVXOKAL-PXAZEXFGSA-N 0.000 claims 1
HLTTZNDUNMRTGX-KDOFPFPSSA-N (6-methoxypyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=CC=C(C=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 HLTTZNDUNMRTGX-KDOFPFPSSA-N 0.000 claims 1
DPEXPEWNJXENAW-PXAZEXFGSA-N (6-methoxypyrimidin-4-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=CC(=NC=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 DPEXPEWNJXENAW-PXAZEXFGSA-N 0.000 claims 1
BSMWQTHOKXWRNJ-IERDGZPVSA-N (6-methyl-3-pyrazol-1-ylpyridin-2-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC1=CC=C(C(=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=C1 BSMWQTHOKXWRNJ-IERDGZPVSA-N 0.000 claims 1
STNGODDQHJMZKH-KDOFPFPSSA-N (7-chloroimidazo[1,2-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC1=CC=2N(C=C1)C(=CN=2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 STNGODDQHJMZKH-KDOFPFPSSA-N 0.000 claims 1
HWMBLPHBACRLRY-IERDGZPVSA-N (7-cyclopropyl-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound C1(CC1)C1=CC(=NC=2N1N=C(C=2)C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 HWMBLPHBACRLRY-IERDGZPVSA-N 0.000 claims 1
KKCXYGXHUCNMDA-KDOFPFPSSA-N (7-fluoroimidazo[1,2-a]pyridin-3-yl)-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC1=CC=2N(C=C1)C(=CN=2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 KKCXYGXHUCNMDA-KDOFPFPSSA-N 0.000 claims 1
GXZPFNAOVAMOBW-KNQAVFIVSA-N (8-aminoquinolin-6-yl)-[(1S,8R)-5-(3,5-difluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound NC=1C=C(C=C2C=CC=NC=12)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC(=C3)F)F)C)[C@@H]1CCC2 GXZPFNAOVAMOBW-KNQAVFIVSA-N 0.000 claims 1
VSBOITAWCYZQLT-UHFFFAOYSA-N 1,5-naphthyridine-2-carbaldehyde Chemical compound N1=CC=CC2=NC(C=O)=CC=C21 VSBOITAWCYZQLT-UHFFFAOYSA-N 0.000 claims 1
KSKFCHXBNMYKDL-UHFFFAOYSA-N 1,6-naphthyridine-5-carbaldehyde Chemical compound C1=CC=C2C(C=O)=NC=CC2=N1 KSKFCHXBNMYKDL-UHFFFAOYSA-N 0.000 claims 1
IDBMXXDFJWXYMN-UZLBHIALSA-N 1-[5-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-diene-12-carbonyl]pyridin-2-yl]cyclopropane-1-carbonitrile Chemical compound CN1N=C2C(=C1C1=CC(=C(C(=C1)F)F)F)C[C@H]1CCC[C@@H]2N1C(=O)C=1C=CC(=NC=1)C1(CC1)C#N IDBMXXDFJWXYMN-UZLBHIALSA-N 0.000 claims 1
BZFYTDHYKDCYCD-IERDGZPVSA-N 1-[5-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-diene-12-carbonyl]pyridin-3-yl]pyrrolidin-2-one Chemical compound CN1N=C2C(=C1C1=CC(=C(C(=C1)F)F)F)C[C@H]1CCC[C@@H]2N1C(=O)C=1C=C(C=NC=1)N1C(CCC1)=O BZFYTDHYKDCYCD-IERDGZPVSA-N 0.000 claims 1
CFIIIUQYTQFNKQ-UHFFFAOYSA-N 1-methylpyrazolo[3,4-b]pyridine-3-carbaldehyde Chemical compound C1=CN=C2N(C)N=C(C=O)C2=C1 CFIIIUQYTQFNKQ-UHFFFAOYSA-N 0.000 claims 1
JPCYNOCAOGYXAY-XIKOKIGWSA-N 1H-benzimidazol-4-yl-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound N1C=NC2=C1C(=CC=C2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 JPCYNOCAOGYXAY-XIKOKIGWSA-N 0.000 claims 1
NBHFAQLRKJGABV-ACJLOTCBSA-N 1H-indazol-7-yl-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound N1N=CC2=CC=CC(=C12)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 NBHFAQLRKJGABV-ACJLOTCBSA-N 0.000 claims 1
SFIPXABGOMYQNR-KUHUBIRLSA-N 1H-indol-7-yl-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound N1C=CC2=CC=CC(=C12)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 SFIPXABGOMYQNR-KUHUBIRLSA-N 0.000 claims 1
WOHQVUYHPVQGAQ-UHFFFAOYSA-N 2-chloro-5-(1,2,4-triazol-4-yl)aniline Chemical compound C1=C(Cl)C(N)=CC(N2C=NN=C2)=C1 WOHQVUYHPVQGAQ-UHFFFAOYSA-N 0.000 claims 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
MBZFOWYEVPOOKN-QRWLVFNGSA-N 3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound O1CCCC2=NC=C(C=C21)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 MBZFOWYEVPOOKN-QRWLVFNGSA-N 0.000 claims 1
GPGPAAGDFXXDND-KUHUBIRLSA-N 6-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-diene-12-carbonyl]pyridine-2-carbonitrile Chemical compound CN1N=C2C(=C1C1=CC(=C(C(=C1)F)F)F)C[C@H]1CCC[C@@H]2N1C(=O)C1=CC=CC(=N1)C#N GPGPAAGDFXXDND-KUHUBIRLSA-N 0.000 claims 1
AKIOQQVCDGVFQN-YKSBVNFPSA-N 6-[(1S,8R)-5-(3,5-difluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-diene-12-carbonyl]-1-(2-fluoroethyl)quinolin-4-one Chemical compound FC=1C=C(C=C(C=1)F)C1=C2C(=NN1C)[C@@H]1CCC[C@H](C2)N1C(=O)C=1C=C2C(C=CN(C2=CC=1)CCF)=O AKIOQQVCDGVFQN-YKSBVNFPSA-N 0.000 claims 1
OMMGAXVUOQTYRZ-QUCCMNQESA-N 6-[(1S,8R)-5-(3,5-difluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-diene-12-carbonyl]-4-methyl-1,4-benzoxazin-3-one Chemical compound FC=1C=C(C=C(C=1)F)C1=C2C(=NN1C)[C@@H]1CCC[C@H](C2)N1C(=O)C1=CC2=C(OCC(N2C)=O)C=C1 OMMGAXVUOQTYRZ-QUCCMNQESA-N 0.000 claims 1
FCXSZHVQQRPVCN-UHFFFAOYSA-N 7-fluoroquinoxaline-6-carbaldehyde Chemical compound FC1=C(C=C2N=CC=NC2=C1)C=O FCXSZHVQQRPVCN-UHFFFAOYSA-N 0.000 claims 1
IPBNQYLKHUNLQE-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid;azane Chemical compound [NH4+].C=12C(S(=O)(=O)[O-])=CC=CC2=CC=CC=1NC1=CC=CC=C1 IPBNQYLKHUNLQE-UHFFFAOYSA-N 0.000 claims 1
101100515514 Arabidopsis thaliana XI-F gene Proteins 0.000 claims 1
DCXBIZUASUMXQQ-VGSWGCGISA-N N-[3-methoxy-5-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-diene-12-carbonyl]phenyl]acetamide Chemical compound COC=1C=C(C=C(C=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)NC(C)=O DCXBIZUASUMXQQ-VGSWGCGISA-N 0.000 claims 1
108091007369 NEUR proteins Proteins 0.000 claims 1
102100030466 Neurocan core protein Human genes 0.000 claims 1
244000086363 Pterocarpus indicus Species 0.000 claims 1
235000009984 Pterocarpus indicus Nutrition 0.000 claims 1
102100028651 Tenascin-N Human genes 0.000 claims 1
101710087911 Tenascin-N Proteins 0.000 claims 1
241001247170 Xana Species 0.000 claims 1
241000607479 Yersinia pestis Species 0.000 claims 1
NKKBLLDDURWFLF-IERDGZPVSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]-quinolin-6-ylmethanone Chemical compound [H][C@]12CC[C@]([H])(N1C(=O)C1=CC=C3N=CC=CC3=C1)C1=NN(C)C(=C1C2)C1=CC(F)=C(F)C(F)=C1 NKKBLLDDURWFLF-IERDGZPVSA-N 0.000 claims 1
UASIYVRGBMZFQF-QRWLVFNGSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]-quinolin-8-ylmethanone Chemical compound [H][C@]12CC[C@]([H])(N1C(=O)C1=CC=CC3=C1N=CC=C3)C1=NN(C)C(=C1C2)C1=CC(F)=C(F)C(F)=C1 UASIYVRGBMZFQF-QRWLVFNGSA-N 0.000 claims 1
HGDHJSATEJUOLI-UZLBHIALSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(2-pyrazol-1-ylpyridin-4-yl)methanone Chemical compound N1(N=CC=C1)C1=NC=CC(=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 HGDHJSATEJUOLI-UZLBHIALSA-N 0.000 claims 1
WEANNUCJQVYULB-IERDGZPVSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(4-pyrazol-1-ylpyridin-2-yl)methanone Chemical compound N1(N=CC=C1)C1=CC(=NC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 WEANNUCJQVYULB-IERDGZPVSA-N 0.000 claims 1
KDMXKJBNBZMCBN-VFNWGFHPSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(4-pyrazol-1-ylpyridin-3-yl)methanone Chemical compound N1(N=CC=C1)C1=C(C=NC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 KDMXKJBNBZMCBN-VFNWGFHPSA-N 0.000 claims 1
DWZCHFFRTPZKOH-IERDGZPVSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(5-propan-2-yloxypyridin-3-yl)methanone Chemical compound C(C)(C)OC=1C=C(C=NC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 DWZCHFFRTPZKOH-IERDGZPVSA-N 0.000 claims 1
AUIQQRPQYBVUAW-IERDGZPVSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(5-pyrazol-1-ylpyridin-3-yl)methanone Chemical compound N1(N=CC=C1)C=1C=C(C=NC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 AUIQQRPQYBVUAW-IERDGZPVSA-N 0.000 claims 1
XXSIWIALDYQTQO-VLIAUNLRSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(6-propan-2-ylpyrimidin-4-yl)methanone Chemical compound C(C)(C)C1=CC(=NC=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 XXSIWIALDYQTQO-VLIAUNLRSA-N 0.000 claims 1
BHUYGBCUWIPUOY-QRWLVFNGSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(6-pyrazol-1-ylpyridin-2-yl)methanone Chemical compound N1(N=CC=C1)C1=CC=CC(=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 BHUYGBCUWIPUOY-QRWLVFNGSA-N 0.000 claims 1
UGYVPNGSRATLKA-UZLBHIALSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(6-pyrazol-1-ylpyridin-3-yl)methanone Chemical compound N1(N=CC=C1)C1=CC=C(C=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 UGYVPNGSRATLKA-UZLBHIALSA-N 0.000 claims 1
OASYIQAYBFOKDP-UTKZUKDTSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(6-pyrrol-1-ylpyridin-3-yl)methanone Chemical compound N1(C=CC=C1)C1=CC=C(C=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 OASYIQAYBFOKDP-UTKZUKDTSA-N 0.000 claims 1
NLQNNVNESZKTPT-VFNWGFHPSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[2-(1,2,4-triazol-4-yl)phenyl]methanone Chemical compound N=1N=CN(C=1)C1=C(C=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 NLQNNVNESZKTPT-VFNWGFHPSA-N 0.000 claims 1
WZIFKSFXBMKMPH-VFNWGFHPSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[2-(triazol-1-yl)phenyl]methanone Chemical compound N1(N=NC=C1)C1=C(C=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 WZIFKSFXBMKMPH-VFNWGFHPSA-N 0.000 claims 1
XKDKCEDYXTXVOP-VLIAUNLRSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[2-(triazol-2-yl)-3-(trifluoromethyl)phenyl]methanone Chemical compound N=1N(N=CC=1)C1=C(C=CC=C1C(F)(F)F)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 XKDKCEDYXTXVOP-VLIAUNLRSA-N 0.000 claims 1
QXEGWMZTYWEQFY-QRWLVFNGSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[2-(triazol-2-yl)-4-(trifluoromethyl)phenyl]methanone Chemical compound N=1N(N=CC=1)C1=C(C=CC(=C1)C(F)(F)F)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 QXEGWMZTYWEQFY-QRWLVFNGSA-N 0.000 claims 1
PJCQKNJCMGYSGN-VFNWGFHPSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[2-(triazol-2-yl)-5-(trifluoromethyl)phenyl]methanone Chemical compound N=1N(N=CC=1)C1=C(C=C(C=C1)C(F)(F)F)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 PJCQKNJCMGYSGN-VFNWGFHPSA-N 0.000 claims 1
MRVZBRAIYIPGHU-KDOFPFPSSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[3-(triazol-2-yl)pyridin-2-yl]methanone Chemical compound N=1N(N=CC=1)C=1C(=NC=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 MRVZBRAIYIPGHU-KDOFPFPSSA-N 0.000 claims 1
YAGVMJYDXFQQNS-QRWLVFNGSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[4-(1,2,4-triazol-4-yl)pyridin-2-yl]methanone Chemical compound N=1N=CN(C=1)C1=CC(=NC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 YAGVMJYDXFQQNS-QRWLVFNGSA-N 0.000 claims 1
HWLKHBGZSPQVCJ-QRWLVFNGSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[5-(1,2,4-triazol-4-yl)pyridin-3-yl]methanone Chemical compound N=1N=CN(C=1)C=1C=C(C=NC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 HWLKHBGZSPQVCJ-QRWLVFNGSA-N 0.000 claims 1
ZEJWYIRSDCXJOC-QRWLVFNGSA-N [(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[5-(triazol-2-yl)pyridin-3-yl]methanone Chemical compound N=1N(N=CC=1)C=1C=C(C=NC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 ZEJWYIRSDCXJOC-QRWLVFNGSA-N 0.000 claims 1
AMVILYUICGNDGE-UZLBHIALSA-N [(1S,8R)-4-methyl-5-phenyl-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]-(1-methylpyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound CN1C=C(C=2C1=NC=CC=2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC=CC=C3)C)[C@@H]1CC2 AMVILYUICGNDGE-UZLBHIALSA-N 0.000 claims 1
BTUQNOJKVBZKIH-GCJKJVERSA-N [(1S,8R)-4-methyl-5-phenyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[2-(1,2,4-triazol-1-yl)phenyl]methanone Chemical compound N1(N=CN=C1)C1=C(C=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC=CC=C3)C)[C@@H]1CCC2 BTUQNOJKVBZKIH-GCJKJVERSA-N 0.000 claims 1
RTERZJOQNPMPAP-IRLDBZIGSA-N [(1S,8R)-4-methyl-5-phenyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[3-(1,2,4-triazol-4-yl)phenyl]methanone Chemical compound N=1N=CN(C=1)C=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC=CC=C3)C)[C@@H]1CCC2 RTERZJOQNPMPAP-IRLDBZIGSA-N 0.000 claims 1
ABQRWYYEZAJLCK-OFNKIYASSA-N [(1S,8R)-5-(3,5-difluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(1-oxidoquinolin-1-ium-6-yl)methanone Chemical compound FC=1C=C(C=C(C=1)F)C1=C2C(=NN1C)[C@@H]1CCC[C@H](C2)N1C(=O)C=1C=C2C=CC=[N+](C2=CC=1)[O-] ABQRWYYEZAJLCK-OFNKIYASSA-N 0.000 claims 1
NHNCPYZDAMDSIT-VGSWGCGISA-N [(1S,8R)-5-(3-chloro-4-methoxyphenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound N=1N(N=CC=1)C1=C(C=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C=C3)OC)Cl)C)[C@@H]1CCC2 NHNCPYZDAMDSIT-VGSWGCGISA-N 0.000 claims 1
FSYNGJIZQRTJGN-GGAORHGYSA-N [(1S,8R)-5-(3-chlorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-(3-pyrazol-1-ylphenyl)methanone Chemical compound N1(N=CC=C1)C=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC=C3)Cl)C)[C@@H]1CCC2 FSYNGJIZQRTJGN-GGAORHGYSA-N 0.000 claims 1
SPEAHADODNSPJL-CTNGQTDRSA-N [(1S,8R)-5-(3-chlorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[1-(3-chlorophenyl)-1,2,4-triazol-3-yl]methanone Chemical compound ClC=1C=C(C=CC=1)N1N=C(N=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC=C3)Cl)C)[C@@H]1CCC2 SPEAHADODNSPJL-CTNGQTDRSA-N 0.000 claims 1
UCWVSSSHPOULGQ-IRLDBZIGSA-N [(1S,8R)-5-(3-chlorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[3-(1,2,4-triazol-1-yl)phenyl]methanone Chemical compound N1(N=CN=C1)C=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC=C3)Cl)C)[C@@H]1CCC2 UCWVSSSHPOULGQ-IRLDBZIGSA-N 0.000 claims 1
GBHNIFLOXGZILO-GGAORHGYSA-N [(1S,8R)-5-(3-chlorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[3-(1H-pyrazol-4-yl)phenyl]methanone Chemical compound N1N=CC(=C1)C=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC=C3)Cl)C)[C@@H]1CCC2 GBHNIFLOXGZILO-GGAORHGYSA-N 0.000 claims 1
XXKMBABMWSXVBU-GCJKJVERSA-N [(1S,8R)-5-(4-fluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound N=1N(N=CC=1)C1=C(C=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC=C(C=C3)F)C)[C@@H]1CCC2 XXKMBABMWSXVBU-GCJKJVERSA-N 0.000 claims 1
XPKYEGDQLHBJPD-QRWLVFNGSA-N [1-(2-methoxyphenyl)-1,2,4-triazol-3-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC1=C(C=CC=C1)N1N=C(N=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 XPKYEGDQLHBJPD-QRWLVFNGSA-N 0.000 claims 1
OAPNJFZJQWEPOA-UZLBHIALSA-N [1-(3-fluorophenyl)-1,2,4-triazol-3-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=C(C=CC=1)N1N=C(N=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 OAPNJFZJQWEPOA-UZLBHIALSA-N 0.000 claims 1
UXTNOTGXPQVVON-IERDGZPVSA-N [1-(3-methoxyphenyl)-1,2,4-triazol-3-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C=C(C=CC=1)N1N=C(N=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 UXTNOTGXPQVVON-IERDGZPVSA-N 0.000 claims 1
HBQVCCALVGCLRW-ACJLOTCBSA-N [1-tert-butyl-5-(trifluoromethyl)pyrazol-4-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound C(C)(C)(C)N1N=CC(=C1C(F)(F)F)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 HBQVCCALVGCLRW-ACJLOTCBSA-N 0.000 claims 1
SMUJAXFFFBWAGB-ZHRRBRCNSA-N [2-(4-methyltriazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC1=NN(N=C1)C1=C(C=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 SMUJAXFFFBWAGB-ZHRRBRCNSA-N 0.000 claims 1
IBICNCNPGNRPLE-UZLBHIALSA-N [2-(5-chloro-1H-1,2,4-triazol-3-yl)phenyl]-[(1S,8R)-5-(3,5-difluorophenyl)-4-methyl-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound ClC1=NC(=NN1)C1=C(C=CC=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=CC(=C3)F)F)C)[C@@H]1CCC2 IBICNCNPGNRPLE-UZLBHIALSA-N 0.000 claims 1
YCFDHNOMWWHEQE-WBMJQRKESA-N [2-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound FC(C=1N=C2N(C=CC=C2)C=1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2)F YCFDHNOMWWHEQE-WBMJQRKESA-N 0.000 claims 1
BJMKJAUWMFZXMB-DYVFJYSZSA-N [2-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC(C=1N=C2N(C=CC=C2)C=1C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)F BJMKJAUWMFZXMB-DYVFJYSZSA-N 0.000 claims 1
QLRHHXHYQKNZPK-XXBNENTESA-N [3-(1-methylpyrazol-4-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CN1N=CC(=C1)C=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 QLRHHXHYQKNZPK-XXBNENTESA-N 0.000 claims 1
WKBUTNQMYFYMIP-GCJKJVERSA-N [3-(4-fluoropyrazol-1-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=NN(C=1)C=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 WKBUTNQMYFYMIP-GCJKJVERSA-N 0.000 claims 1
GFLTUKCQSILKKZ-JPYJTQIMSA-N [3-(4-methoxypyrazol-1-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C=NN(C=1)C=1C=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 GFLTUKCQSILKKZ-JPYJTQIMSA-N 0.000 claims 1
DTTKPYHUDABKDU-VLIAUNLRSA-N [3-fluoro-2-(1,2,4-triazol-1-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C(=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CN=C1 DTTKPYHUDABKDU-VLIAUNLRSA-N 0.000 claims 1
IEKUSQDQFFMKNX-VLIAUNLRSA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C(=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 IEKUSQDQFFMKNX-VLIAUNLRSA-N 0.000 claims 1
RYVHLCZBIVILJL-IERDGZPVSA-N [3-fluoro-5-(1,2,4-triazol-4-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=C(C=C(C=1)N1C=NN=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 RYVHLCZBIVILJL-IERDGZPVSA-N 0.000 claims 1
VLTSBNJWZWWQDD-QRWLVFNGSA-N [3-methoxy-2-(triazol-1-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C(=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=NC=C1 VLTSBNJWZWWQDD-QRWLVFNGSA-N 0.000 claims 1
UCHBKKSHFMPYMC-QRWLVFNGSA-N [3-methoxy-2-(triazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C(=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 UCHBKKSHFMPYMC-QRWLVFNGSA-N 0.000 claims 1
ILGCAPJQUOFKIK-IERDGZPVSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC=1C(=C(C=CC=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 ILGCAPJQUOFKIK-IERDGZPVSA-N 0.000 claims 1
NKJZSRRTCWOSNM-QRWLVFNGSA-N [4-fluoro-2-(1,2,4-triazol-1-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC1=CC(=C(C=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CN=C1 NKJZSRRTCWOSNM-QRWLVFNGSA-N 0.000 claims 1
SQGVYFNSRZTARU-QRWLVFNGSA-N [4-fluoro-2-(triazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC1=CC(=C(C=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 SQGVYFNSRZTARU-QRWLVFNGSA-N 0.000 claims 1
RCAGAILWWRIITL-QRWLVFNGSA-N [4-fluoro-3-(1,2,4-triazol-4-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC1=C(C=C(C=C1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1C=NN=C1 RCAGAILWWRIITL-QRWLVFNGSA-N 0.000 claims 1
NWMRUPWIFRKUPF-BZNIZROVSA-N [5-(difluoromethyl)-1-methylpyrazol-4-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC(C1=C(C=NN1C)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)F NWMRUPWIFRKUPF-BZNIZROVSA-N 0.000 claims 1
KIYFMEBGRDOBMX-VFNWGFHPSA-N [5-fluoro-2-(1,2,4-triazol-1-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound FC=1C=CC(=C(C=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CN=C1 KIYFMEBGRDOBMX-VFNWGFHPSA-N 0.000 claims 1
STJVWUYZONMQCK-QRQCRPRQSA-N [5-methoxy-2-(1,2,4-triazol-1-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C=CC(=C(C=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CN=C1 STJVWUYZONMQCK-QRQCRPRQSA-N 0.000 claims 1
IOECBWNHQRIVDY-QRQCRPRQSA-N [5-methoxy-2-(triazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound COC=1C=CC(=C(C=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 IOECBWNHQRIVDY-QRQCRPRQSA-N 0.000 claims 1
OCMAOQYMABIBSW-ZHRRBRCNSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC=1C=CC(=C(C=1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 OCMAOQYMABIBSW-ZHRRBRCNSA-N 0.000 claims 1
DHJQQZUIAOKNOQ-QRWLVFNGSA-N [6-methyl-3-(1,2,4-triazol-1-yl)pyridin-2-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC1=CC=C(C(=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CN=C1 DHJQQZUIAOKNOQ-QRWLVFNGSA-N 0.000 claims 1
JZBSYAWPULCYNA-BEFAXECRSA-N [6-methyl-3-(triazol-2-yl)pyridin-2-yl]-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound CC1=CC=C(C(=N1)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2)N1N=CC=N1 JZBSYAWPULCYNA-BEFAXECRSA-N 0.000 claims 1
239000002131 composite material Substances 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
ZJLFAZIRJZCPPQ-UHFFFAOYSA-N furo[3,2-b]pyridine-6-carbaldehyde Chemical compound O=CC1=CN=C2C=COC2=C1 ZJLFAZIRJZCPPQ-UHFFFAOYSA-N 0.000 claims 1
DUQBATTVGHATOI-PXAZEXFGSA-N furo[3,2-c]pyridin-4-yl-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,11-triazatricyclo[6.2.1.02,6]undeca-2,5-dien-11-yl]methanone Chemical compound O1C=CC=2C(=NC=CC=21)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CC2 DUQBATTVGHATOI-PXAZEXFGSA-N 0.000 claims 1
UFYDDMNFSPEGFZ-KDOFPFPSSA-N imidazo[1,2-a]pyridin-3-yl-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound N=1C=C(N2C=1C=CC=C2)C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 UFYDDMNFSPEGFZ-KDOFPFPSSA-N 0.000 claims 1
IXVGKARTGQSQOW-KDOFPFPSSA-N imidazo[1,2-a]pyridin-5-yl-[(1S,8R)-4-methyl-5-(3,4,5-trifluorophenyl)-3,4,12-triazatricyclo[6.3.1.02,6]dodeca-2,5-dien-12-yl]methanone Chemical compound N=1C=CN2C=1C=CC=C2C(=O)N1[C@H]2CC=3C(=NN(C=3C3=CC(=C(C(=C3)F)F)F)C)[C@@H]1CCC2 IXVGKARTGQSQOW-KDOFPFPSSA-N 0.000 claims 1
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VCJVHCAMIHYKKA-UHFFFAOYSA-N methyl 4-bromopyridine-3-carboxylate;hydrobromide Chemical compound Br.COC(=O)C1=CN=CC=C1Br VCJVHCAMIHYKKA-UHFFFAOYSA-N 0.000 description 1
HSNLSLNACLYWKJ-UHFFFAOYSA-N methyl 4-iodopyridine-2-carboxylate Chemical compound COC(=O)C1=CC(I)=CC=N1 HSNLSLNACLYWKJ-UHFFFAOYSA-N 0.000 description 1
UOJBQBKTXIRLDP-UHFFFAOYSA-N methyl 5-(triazol-1-yl)pyridine-3-carboxylate Chemical compound N1(N=NC=C1)C=1C=C(C=NC=1)C(=O)OC UOJBQBKTXIRLDP-UHFFFAOYSA-N 0.000 description 1
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QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical class COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
BVQIGDNWKHPLOE-UHFFFAOYSA-N methyl indolizine-7-carboxylate Chemical compound C1=C(C(=O)OC)C=CN2C=CC=C21 BVQIGDNWKHPLOE-UHFFFAOYSA-N 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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239000002687 nonaqueous vehicle Substances 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
229960002969 oleic acid Drugs 0.000 description 1
230000005959 oncogenic signaling Effects 0.000 description 1
229940005483 opioid analgesics Drugs 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
201000008016 ovarian benign neoplasm Diseases 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
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UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
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208000019906 panic disease Diseases 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
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239000000825 pharmaceutical preparation Substances 0.000 description 1
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DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
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235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
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229910000160 potassium phosphate Inorganic materials 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
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230000003518 presynaptic effect Effects 0.000 description 1
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235000019260 propionic acid Nutrition 0.000 description 1
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JGQDBVXRYDEWGM-UHFFFAOYSA-N quinoxaline-6-carboxylic acid Chemical compound N1=CC=NC2=CC(C(=O)O)=CC=C21 JGQDBVXRYDEWGM-UHFFFAOYSA-N 0.000 description 1
239000002469 receptor inverse agonist Substances 0.000 description 1
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230000001105 regulatory effect Effects 0.000 description 1
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230000004044 response Effects 0.000 description 1
210000003994 retinal ganglion cell Anatomy 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
238000007614 solvation Methods 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
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239000011975 tartaric acid Substances 0.000 description 1
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150000003892 tartrate salts Chemical class 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
URLYINUFLXOMHP-HTVVRFAVSA-N tcn-p Chemical compound C=12C3=NC=NC=1N(C)N=C(N)C2=CN3[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O URLYINUFLXOMHP-HTVVRFAVSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
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LZHVQDKGQDBPPN-UHFFFAOYSA-J tetrapotassium disulfate Chemical compound S(=O)(=O)([O-])[O-].S(=O)(=O)([O-])[O-].[K+].[K+].[K+].[K+] LZHVQDKGQDBPPN-UHFFFAOYSA-J 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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GLUUKBVZIQVGQX-UHFFFAOYSA-N triazolo[1,5-a]pyridine-5-carboxylic acid Chemical compound C1=C(C(=O)O)C=CN2N=NC=C21 GLUUKBVZIQVGQX-UHFFFAOYSA-N 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
BUJKNFNMGRYZBV-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+);hydrate Chemical compound O.[Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F BUJKNFNMGRYZBV-UHFFFAOYSA-K 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

BR112021005936-9A 2018-09-28 2019-09-27 moduladores de monoacilglicerol lipase BR112021005936A2 (pt)

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US62/738,684		2018-09-28
PCT/IB2019/058241 WO2020065614A1 (en)	2018-09-28	2019-09-27	Monoacylglycerol lipase modulators

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EP (1)	EP3856179A1 (es)
JP (2)	JP7413368B2 (es)
KR (1)	KR20210069079A (es)
CN (1)	CN113164458A (es)
AU (1)	AU2019349962A1 (es)
BR (1)	BR112021005936A2 (es)
CA (1)	CA3111309A1 (es)
MA (1)	MA53722A (es)
MX (1)	MX2021003661A (es)
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2019
- 2019-09-27 EP EP19780428.9A patent/EP3856179A1/en active Pending
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- 2019-09-27 JP JP2021517338A patent/JP7413368B2/ja active Active
- 2019-09-27 CA CA3111309A patent/CA3111309A1/en active Pending
- 2019-09-27 KR KR1020217012861A patent/KR20210069079A/ko unknown
- 2019-09-27 MA MA053722A patent/MA53722A/fr unknown
- 2019-09-27 BR BR112021005936-9A patent/BR112021005936A2/pt unknown
- 2019-09-27 CN CN201980078966.8A patent/CN113164458A/zh active Pending
- 2019-09-27 US US16/586,263 patent/US20200102311A1/en not_active Abandoned
- 2019-09-27 TW TW108135034A patent/TW202035409A/zh unknown
2020
- 2020-12-23 US US17/132,406 patent/US11597728B2/en active Active
2023
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KR20210069079A (ko)	2021-06-10
MA53722A (fr)	2022-03-30
US20230242531A1 (en)	2023-08-03
EP3856179A1 (en)	2021-08-04
US20220315583A1 (en)	2022-10-06
JP7413368B2 (ja)	2024-01-15
JP2024038151A (ja)	2024-03-19
MX2021003661A (es)	2021-08-19
CN113164458A (zh)	2021-07-23
US20200102311A1 (en)	2020-04-02
CA3111309A1 (en)	2020-04-02
WO2020065614A1 (en)	2020-04-02
JP2022502440A (ja)	2022-01-11
AU2019349962A1 (en)	2021-03-18
TW202035409A (zh)	2020-10-01
US11597728B2 (en)	2023-03-07

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